1. Rico (Little Caesar)
Enrico Cesare Bandello (a.k.a. Rico, a.k.a. Little Caesar) portrayed by Edward G. Robinson was one of Hollywood’s first famous gangster characters. Little Caesar hit the silver screen in 1931 and is noted as the first large-scale gangster movie of its genre—a gangster film that focused on the rise and fall of the gangster.
2. Tom Powers (The Public Enemy)
James Cagney stepped into the role of gangster Tom Powers in the 1931 Warner Bros. release of The Public Enemy. The ambitious, ruthless Tom Powers still resonates on screen more than 80 years later. He will always be remembered as the gangster who smashed a grapefruit into Mae Clarke’s stunning face.
3. Vito Corleone (The Godfather)
The head of the Corleone crime family, Vito Corleone, (played by Marlon Brando) was the most powerful mafia boss who lived by a strict code of honor and placed the highest regard upon family values. With business interests that included bootlegging, gambling and union corruption, Vito was not a man to cross. Marlon Brando won the Oscar for Best Actor in a Leading Role for his portrayal of Vito Corleone.
4. Michael Corleone (The Godfather)
Portrayed by Al Pacino, the character of Michael Corleone over the course of the Godfather trilogy has the most definitive transformation. Michael begins as a war hero but after the murders of his brother and father, he steps into the center ring as head of the Corleone family.
5. Tony Montana (Scarface)
Brian DePalma’s 1983 rendition of Scarface cast the seasoned Al Pacino as Tony Montana. Montana’s anger and aggressively violent behavior help to easily land him on many lists of ultimate gangsters. Who can ever forget Tony and his “little friend” machine gun?
6. Tommy DeVito (Goodfellas)
Joe Pesci won the Oscar for Best Actor in a Supporting Role for his unforgettable screen presence as Tommy DeVito in the 1990 movie, Goodfellas. Aggressive, short-tempered and explosively violent, Tommy DeVito is as quick with his gun as he is with his favorite four-letter word.
7. Benjamin “Lefty” Ruggiero (Donnie Brasco)
Al Pacino plays yet another of the great film gangsters—Lefty Ruggiero. Based on a true story, Ruggiero is a mobster who takes a young Donnie Brasco (who is actually an undercover agent) under his wing and introduces him to a world of crime.
8. Frank Lucas (American Gangster)
Frank Lucas rose to become one the most powerful crime bosses in Harlem in the 1970’s. Based on the real heroin kingpin Frank Lucas, actor Denzel Washington portrayed Lucas on-screen, creating one of the most vibrant gangster portrayals of all time.
9. Jack Carter (Get Carter)
London gangster Jack Carter, played by Michael Caine in this 1971 film, is a single-minded, ruthless killing machine. Determined to uncover the truth behind his brother’s death, nothing gets in the way of Jack Carter.
10. Al Capone (The Untouchables)
Brilliant Robert De Niro played Al Capone – one of the most ruthless gangsters in American history, infamous for his criminal career that included multiple counts of murder, extortion and corruption.